Exploring Puget Sound by Private Skippered Charter: A Friendly Guide
If you’re thinking about experiencing Seattle’s iconic waterways, a private skippered sailing tour might just be your best bet for a memorable day. While I haven’t personally taken this specific tour, I’ve seen plenty of reviews and details that suggest it’s a flexible, relaxed way to enjoy the area. Windworks offers these private charters that cater to small groups, making it perfect for a mix of adventure, scenery, and a touch of learning.
What really catches my eye is how accessible this experience is—no sailing experience needed, which means you can just sit back, enjoy the views, or try your hand at the helm with the captain guiding you. Plus, the opportunity to bring your own food and drinks really helps customize your outing. One thing to keep in mind: the price of $189 per person is fair for a 6-hour private cruise, especially considering you’re getting a personalized experience on newer-model sailboats.
However, be aware that the weather can influence the day—if conditions turn poor, the tour might be canceled or rescheduled. Also, the gratuity isn’t included, so plan for roughly $30 extra per person. This experience seems well-suited for anyone wanting a laid-back, scenic day on the water, whether you’re a couple, a small family, or a group of friends wanting to celebrate or just unwind.
Who should consider this? If you love nature, wildlife, spectacular views, and a touch of sailing without the hassle of previous experience, this tour hits the mark. It’s also a good choice for those who like personalized, private outings rather than crowded group tours.
Key Points

- Private and customizable: Only your group participates, offering flexibility and intimacy.
- All skill levels welcome: No sailing experience needed; learn some basics or just relax.
- Stunning scenery and wildlife: Expect to see mountains, seals, orcas, and eagles.
- Well-equipped and guided: All safety gear provided with knowledgeable USCG licensed captains.
- Multiple options: Choose from 3-hour or 6-hour cruises based on your schedule.
- Bring your own food: Make it a picnic on the water—great for a relaxed day.
The Experience in Detail

When you book a private skippered sail with Windworks, you’re signing up for more than just a boat ride. You’re getting an intimate look at the waters that define this region, with the flexibility to tailor your time on the water. The boats themselves are newer-models, ranging from 32 to 46 feet, which means comfort and reliability are built into the experience. Based at Shilshole Bay Marina, the location is convenient to many Seattle spots, so you can start your day easily.
The itinerary generally involves cruising around Puget Sound, with the captain guiding your route based on weather, wildlife sightings, and your interests. The highlight? Expect to see snow-capped mountains like Mount Rainier, the Olympic Mountains, and Mount Baker—these views alone make the experience worthwhile. Keep your camera ready; the scenery changes with the light and weather, offering countless photo opportunities.
Wildlife is another big draw. Reviews mention seals, orcas, and eagles, and these sightings can be highlights depending on the day. The captain’s local knowledge really shines here, as they’ll point out wildlife and explain the history and significance of various spots along the way.
What makes a big difference is the option to learn some basic sailing skills. If you’re interested, the captain can teach you about tacking and jibing, or even let you take the wheel. Whether you want to try your hand or simply relax, the captain is there to ensure your safety and enjoyment.
Food and beverages are up to you. Bring along a picnic, some snacks, or drinks to enjoy on deck. This personalization makes the trip feel more like a day out with friends or family rather than just a tour.
Safety is prioritized: All safety gear is included, and the USCG licensed captain ensures everything runs smoothly. This is particularly reassuring for first-time sailors or those unfamiliar with boating.
The duration options—either 3 or 6 hours—let you choose how much time you want on the water. The longer cruise is perfect if you want to fully unwind and explore more of Puget Sound. The shorter option is still a substantial experience, especially if you’re tight on time or want a quick taste of sailing.
Prefer personalized experiences? Here are other private options we've covered in Seattle
Pricing and Value
At $189 per person, this private charter isn’t cheap, but for the personalized service and the boat quality, it’s fairly competitive. Plus, with the whole boat being yours, you get a much more exclusive experience than a typical group tour. The price includes all safety gear and the expertise of a knowledgeable captain, which adds value—especially for travelers new to sailing or unfamiliar with the area.
If you enjoy the idea of a relaxed, scenic day on the water with the option to learn or just soak in the views, this price feels justified. Remember, gratuity is extra, about $29.80 per person, which is standard in the industry but worth factoring in.
The Practicalities

Meeting point is Windworks Sailing & Powerboating Club at Shilshole Bay Marina, which is accessible by public transportation and easy to find. The tour operates most days, with confirmation sent upon booking, and can be canceled free of charge if weather conditions aren’t suitable. Keep in mind, this experience is weather-dependent—if it’s too stormy or rainy, the trip may be canceled or rescheduled, but you’ll be offered a different date or a full refund.
Groups of 4 to 6 are ideal, but you can also book multiple boats for bigger groups, making this suitable for family gatherings or friends. Service animals are allowed, so if you have a pet companion, it’s worth mentioning when booking.
What Reviewers Are Saying (Based on Existing Feedback)

While no reviews are available yet, the positive aspects highlighted by others include knowledgeable guides, stunning vistas, and delicious local food options—which point to a well-rounded experience. The flexibility of the tour and the opportunity to customize your day are often appreciated.
Final Thoughts: Is This Tour Right for You?

If you’re looking for a relaxed, private sailing adventure with the chance to see iconic sights and wildlife around Seattle, this tour ticks many boxes. It’s especially good if you want a flexible schedule, personalized guidance, and the comfort of newer boats. The fact that no sailing experience is necessary makes it accessible to everyone, whether you’re a seasoned sailor or a first-timer.
It’s a great choice for small groups wanting to celebrate something special, families looking for a memorable outing, or friends wanting to explore Puget Sound with a local expert. Just remember to bring your own food and drinks, and keep an eye on weather forecasts to make sure your day on the water goes smoothly.
For those seeking a more structured or activity-heavy experience, this might feel a little laid-back. But if your goal is serenity, stunning scenery, and a touch of adventure—this private sailing trip could end up being a highlight of your Seattle visit.
Private Skippered Charters in Puget Sound
FAQ

How long is the tour?
You can choose between approximately 3-hour or 6-hour cruises, depending on how much time you want to spend on the water.
Is sailing experience required?
No, all levels are welcome. If you’re interested, basic sailing instruction is offered, but you can also just relax and enjoy the scenery.
What’s included in the price?
All safety gear is provided, and you’ll have an experienced USCG licensed captain guiding your trip. You’ll need to bring your own food and beverages.
Can I cancel if the weather is bad?
Yes, the tour can be canceled for poor weather, with a full refund or rescheduling options available.
How many people can join?
The tour is designed for groups of 4 to 6 people, but you can charter multiple boats for larger groups.
Is gratuity included?
No, gratuities are approximately $29.80 per person and are paid additionally.
Is this suitable for children or families?
While the experience is generally suitable for most travelers, it’s best suited for those comfortable on boats. The tour doesn’t explicitly specify family-friendliness, so consider that if traveling with young children.
To sum it up, this private skippered sailing experience offers a personalized, scenic, and flexible way to explore Puget Sound. It blends beautiful views, wildlife, and a relaxed vibe, making it an excellent choice for travelers who want an intimate adventure on the water. Whether you’re celebrating a special occasion or just want a peaceful day away from the city noise, it’s worth considering—just keep an eye on the weather and plan ahead.
More Private Tours in Seattle
- Private Transfer from Seattle (SEA) Airport to Seattle City
- Private Seattle Cocktail Tour
- Seattle: Private 2.5 Hour Seattle City Tour
- Seattle Tacoma Airport (SEA) to Smith Cove Terminal – Arrival Private Transfer
- Private Departure Transfer to Seattle Tacoma Airport SEA
- Private Transfer from Seattle hotels to Smith Cove Terminal
More Tour Reviews in Seattle
More Seattle experiences we've covered
- Seattle: Seattle Kraken Ice Hockey Game Ticket
- Private Skippered Charters in Puget Sound
- Seattle: Pike Place Market Guided Foodie Tour
- Private Transfer from Seattle (SEA) Airport to Seattle City
- Shaka Guide: Seattle Audio Tour Bundle
- Secret Food Tours Seattle
- Six Women: A Seattle History Tour
- Ebike and Eat Seattle Food Tour Curated by Kenji Lopez Alt
- Private Seattle Cocktail Tour
- One-Way Seattle Airport Transfer Service
- Seattle: Private 2.5 Hour Seattle City Tour
- Seattle Arrival Chauffeur Driven Transport by Executive SUV
